Naringenin

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Naringenin
Naringenin.svg
Naringenin 3D BS.png
Names
IUPAC name
(2S)-4′,5,7-Trihydroxyflavan-4-one
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Naringetol; Salipurol; Salipurpol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.865 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 X mark.svgN
    Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N X mark.svgN
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
Properties
C15H12O5
Molar mass 272.256 g·mol−1
Melting point 251 °C (484 °F; 524 K) [1]
475 mg/L[ citation needed ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Naringenin is a flavanone from the flavonoid group of polyphenols. [2] It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. [2]

Contents

The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. [2] High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. [2] Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs. [2]

Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications. [2] [3] [4] [5]

Structure

Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4′, 5, and 7 carbons. [2] It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7.

Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable. [6] [7] Racemization of (S)-(−)-naringenin has been shown to occur fairly quickly. [8]

Sources and bioavailability

Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit, oranges, and lemons, [2] sour orange, [9] sour cherries, [10] tomatoes, [11] cocoa, [12] Greek oregano, [13] water mint, [14] as well as in beans. [15] Ratios of naringenin to naringin vary among sources, [2] as do enantiomeric ratios. [7]

The naringenin-7-glucoside form seems less bioavailable than the aglycol form. [16]

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice. [17]

Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste. [18]

Biosynthesis and metabolism

Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase. [2] Naringenin is derived from malonyl-CoA and 4-coumaroyl-CoA. [2] The latter is derived from phenylalanine. The resulting tetraketide is acted on by chalcone synthase to give the chalcone that then undergoes ring-closure to naringenin. [19]

The enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2S)-naringenin to produce diphosphate and 8-prenylnaringenin. Cunninghamella elegans , a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation. [20]

Metabolic fate and research

The fate and biological roles of naringenin are difficult to study because naringenin is rapidly metabolized in the intestine and liver, and its metabolites are destined for excretion. [2] [21] The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound. [2] [21]

Related Research Articles

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">CYP3A4</span> Enzyme that metabolizes substances by oxidation

Cytochrome P450 3A4 is an important enzyme in the body, mainly found in the liver and in the intestine, which in humans is encoded by CYP3A4 gene. It oxidizes small foreign organic molecules (xenobiotics), such as toxins or drugs, so that they can be removed from the body. It is highly homologous to CYP3A5, another important CYP3A enzyme.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.

<span class="mw-page-title-main">Quercetin</span> Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Naringin</span> Chemical compound

Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness (debittering) created by naringin. In humans naringin is metabolized to the aglycone naringenin by naringinase present in the gut.

Grapefruit seed extract (GSE), also known as citrus seed extract, is a liquid extract derived from the seeds, pulp, and white membranes of grapefruit. GSE is prepared by grinding the grapefruit seed and juiceless pulp, then mixing with glycerin. Commercially available GSEs sold to consumers are made from the seed, pulp, and glycerin blended together. GSE is sold as a dietary supplement and is used in cosmetics.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">Hesperetin</span> Chemical compound

Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. The 7-O-glycoside of hesperetin, hesperidin, is a naturally occurring flavanone-glycoside, the main flavonoid in grapefruits, lemons, and sweet oranges.

<span class="mw-page-title-main">Grapefruit–drug interactions</span> Drug interactions with grapefruit juice

Some fruit juices and fruits can interact with numerous drugs, in many cases causing adverse effects. The effect is most studied with grapefruit and grapefruit juice, but similar effects have been observed with certain other citrus fruits.

<span class="mw-page-title-main">Flavones</span> Class of flavonoid chemical compounds

Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Naringinase is a debittering enzyme that is used in the commercial production of citrus juices. It breaks down the compound naringin that gives citrus juices its bitter taste. It is a multienzyme complex which possesses alpha-L-rhamnosidase and beta glucosidase active centers. The E.C. No.(EC 3.2.1.40) of the naringinase and rhamnosidase are the same. First rhamnosidase breaks naringin into prunin and rhamnose. Lastly glucosidase breaks prunin into glucose and naringenin, a flavorless flavanone also found in various citrus.

<span class="mw-page-title-main">Flavanone</span>

The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides.

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

In enzymology, a flavanone 7-O-beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Chalconoid</span> Natural phenols related to chalcone

Chalconoids, also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important biological compounds.

<span class="mw-page-title-main">Narirutin</span> Chemical compound

Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose.

<span class="mw-page-title-main">Melitidin</span> Chemical compound

Melitidin is a flavanone glycoside. Melitidin was discovered in bergamot orange juice and exhibits statin-like properties in preclinical research.

<span class="mw-page-title-main">Prunin</span> Chemical compound

Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin.

References

  1. ↑ Naringenin at the Human Metabolome Database
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024.
  3. ↑ Lohezic-Le Devehat, F.; Marigny, K.; Doucet, M.; Javaudin, L. (2002). "[Grapefruit juice and drugs: a hazardous combination?]". Therapie. 57 (5): 432–445. ISSN   0040-5957. PMID   12611197.
  4. ↑ Singh, B. N. (September 1999). "Effects of food on clinical pharmacokinetics". Clinical Pharmacokinetics. 37 (3): 213–255. doi:10.2165/00003088-199937030-00003. ISSN   0312-5963. PMID   10511919.
  5. ↑ Fuhr, U. (April 1998). "Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance". Drug Safety. 18 (4): 251–272. doi:10.2165/00002018-199818040-00002. ISSN   0114-5916. PMID   9565737.
  6. ↑ Yáñez JA, Andrews PK, Davies NM (April 2007). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 848 (2): 159–181. doi:10.1016/j.jchromb.2006.10.052. PMID   17113835.
  7. 1 2 Yáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM (March 2008). "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices". Biopharmaceutics & Drug Disposition. 29 (2): 63–82. doi:10.1002/bdd.588. PMID   18058792. S2CID   24051610.
  8. ↑ Krause M, Galensa R (July 1991). "Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase". Chromatographia. 32 (1–2): 69–72. doi:10.1007/BF02262470. ISSN   0009-5893. S2CID   95215634.
  9. ↑ Gel-Moreto N, Streich R, Galensa R (August 2003). "Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis". Electrophoresis. 24 (15): 2716–2722. doi:10.1002/elps.200305486. PMID   12900888. S2CID   40261445.
  10. ↑ Wang H, Nair MG, Strasburg GM, Booren AM, Gray JI (March 1999). "Antioxidant polyphenols from tart cherries (Prunus cerasus)". Journal of Agricultural and Food Chemistry. 47 (3): 840–844. doi:10.1021/jf980936f. PMID   10552377.
  11. ↑ Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P, Martín Belloso O (September 2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields". Journal of Agricultural and Food Chemistry. 60 (38): 9667–9672. doi:10.1021/jf302791k. PMID   22957841.
  12. ↑ Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM (January 2003). "Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao)". Journal of Mass Spectrometry. 38 (1): 35–42. Bibcode:2003JMSp...38...35S. doi:10.1002/jms.395. PMID   12526004.
  13. ↑ Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (November 2003). "LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano". Analytical Chemistry. 75 (22): 6288–6294. doi:10.1021/ac0347819. PMID   14616013.
  14. ↑ Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK (May 2008). "Isolation of the MAO-inhibitor naringenin from Mentha aquatica L". Journal of Ethnopharmacology. 117 (3): 500–502. doi:10.1016/j.jep.2008.02.015. PMID   18372132.
  15. ↑ Hungria M, Johnston AW, Phillips DA (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli". Molecular Plant-Microbe Interactions. 5 (3): 199–203. doi:10.1094/mpmi-5-199. PMID   1421508.
  16. ↑ Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA (November 1999). "Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation". Biochemical and Biophysical Research Communications. 265 (2): 410–415. doi:10.1006/bbrc.1999.1695. PMID   10558881.
  17. ↑ Erlund I, Meririnne E, Alfthan G, Aro A (February 2001). "Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice". The Journal of Nutrition. 131 (2): 235–241. doi: 10.1093/jn/131.2.235 . PMID   11160539.
  18. ↑ Bugianesi R, Catasta G, Spigno P, D'Uva A, Maiani G (November 2002). "Naringenin from cooked tomato paste is bioavailable in men". The Journal of Nutrition. 132 (11): 3349–3352. doi: 10.1093/jn/132.11.3349 . PMID   12421849.
  19. ↑ Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668. doi:10.1021/acs.jafc.6b05212. PMID   28168876.
  20. ↑ Ibrahim AR (January 2000). "Sulfation of naringenin by Cunninghamella elegans". Phytochemistry. 53 (2): 209–212. Bibcode:2000PChem..53..209I. doi:10.1016/S0031-9422(99)00487-2. PMID   10680173.
  21. 1 2 Rothwell JA, Urpi-Sarda M, Boto-Ordoñez M, Llorach R, Farran-Codina A, Barupal DK, Neveu V, Manach C, Andres-Lacueva C, Scalbert A (January 2016). "Systematic analysis of the polyphenol metabolome using the Phenol-Explorer database". Molecular Nutrition & Food Research. 60 (1): 203–11. doi:10.1002/mnfr.201500435. PMC   5057353 . PMID   26310602.
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